Patent GB-1108416-A (GB)
Title: Triazolyl-stilbene brightening agents
Inventor: DORLARS ALFONS
IPC: C07D249/16
Filed: 1966-05-20
Abstract: Brightened polyamides are prepared in Example 9 by mixing e -caprolactam, e -aminocaproic acid, acetic acid, titanium dioxide and various brightening agents covered by the general formula <FORM:1108416/C3/1> wherein R1 is H, or substituted or unsubstituted alkyl or aryl, R2 is substituted or unsubstituted alkyl or aryl, or R1 + R2 + the two carbon atoms of the triazole ring form a non-aromatic ring system; X1 and X2 are H, -SO3H, sulphonic ester, substituted or unsubstituted sulphonamide, alkyl or aryl sulphone, -COOH, ester, substituted or unsubstituted amide or -CN substituents and Y is H, an acylated amino group or a substituted or unsubstituted triazolyl or pyrazolyl group or their alkali metal salts and heating the mixture to 260 DEG  C.  Polyvinyl chloride is brightened in Example 10 by various brightening agents covered by the general formula above.ALSO:Soaps and detergents may be brightened by addition of a brightening agent of formula <FORM:1108416/C4-C5/1> wherein R1 is H or substituted or unsubstituted alkyl or aryl, R2 is substituted or unsubstituted alkyl or aryl or R1 + R2 + the two carbon atoms of the triazole ring form a non-aromatic ring system; X1 and X2 are H, -SO3H, sulphonic ester, substituted or unsubstituted sulphonamide, alkyl or aryl sulphone, carboxylic acid or ester, substituted or unsubstituted amide, or -CN substituents; and Y is H, acylated amino group or a substituted or unsubstituted triazolyl or pyrazolyl group or their alkali metal salts.  Example 4 describes compositions containing granulated soap and Example 5, compositions containing an anionactive detergent with the brightening agents above.ALSO:The invention comprises 1,2,3-triazolyl-(2)-stilbenes of formula <FORM:1108416/C2/1> wherein R1 is H, or an alkyl or aryl group which both may be substituted by e.g. -SO3H, alkoxy, carboxylic, or halogen, substituents, R2 is alkyl or aryl which may be similarly substituted, or R1 and R2 together with the two carbon atoms of the triazole ring may form a non-aromatic ring system; X1 and X2 are H, SO3H, sulphonic ester, substituted or unsubstituted sulphonamide, alkyl or aryl sulphones, carboxylic, ester, substituted or unsubstituted amide or -CN substituents; and Y is M or an acylated amino group or a substituted or unsubstituted triazolyl or pyrazolyl group, and including the sodium salts of sulphonic acid groups when present. The compounds may be prepared by (i) in the case of symmetrical compounds of Formula I condensating a compound <FORM:1108416/C2/2> with an a -oximino-ketone of formula <FORM:1108416/C2/3> or <FORM:1108416/C2/4> wherein Z is H or an acyl group and converting the resultant bis-a -oximino-hydrazone into the symonetric bis - [triazolyl - (2)] - stilbene by splitting off HOZ; (ii) in the case of asymmetrical compounds I, by condensing a compound <FORM:1108416/C2/5> wherein W is a group convertible to a free amino group e.g. -NO2 or acylamino, with III or IV above, converting the resultant a -oximino-hydrazone into the triazolyl - (2)-stilbene by splitting off HOZ and then transforming W into the desired substituent Y.  In some examples, symmetrical products are modified by sulphonation, replacement of a methoxy group by a carboxymethoxy group (cf. Examples 2 and 9), and formation of a carboxylic group (cf. Examples 6 and 9).  Example 5 describes the reduction of a nitro group in a symmetrical compound to an amino group which is then acylated with e.g. anisoyl chloride, diazotized and reduced to the hydrazine group and condensed with phenylmalondialdehyde, or converted to a triazolyl group by diazotizing the amino group, coupling the diazo compound with 2 - naphthylamine - 5 - sulphonic acid and oxidizing the azo-dyestuff formed.  Sulphonamide or sulphonic ester groups may be introduced at X1 or X2 by converting the correspondin sulphonic acid into the sulphonyl chloride which is then reacted with an amine or an hydroxy compound (cf. Example 10).ALSO:The invention comprises brightening agents useful for brightening cotton, paper, wool and fibres, foils or filaments made from polyamides, polyesters, polyacrylonitrile, polyvinyl chloride and cellulose acetates, having the formula:- <FORM:1108416/D1-D2/1> wherein R1 is H or substituted or unsubstituted alkyl or aryl, R2 is substituted or unsubstituted alkyl or aryl, or R1 + R2 + the two carbon atoms of the triazole ring form a non-aromatic ring system; X1 and X2 are H,-SO3H, sulphonic ester, substituted or unsubstituted sulphonamide, alkyl or aryl sulphone, -COOH, ester, substituted or unsubstituted amide or -CN substituents, and Y is H, an acylated amino group or a substituted or unsubstituted triazolyl or pyrazolyl group, or the alkali metal salts of said compound.